An activity-guided isolation study on the EtOH extract prepared from the bulbs of Prospero autumnale yielded four new phenolic compounds, including a new stilbenoid (1), a new homoisoflavonoid derivative (8), a new homoisoflavonoid dimer (9), and an unprecedented homoisoflavone-stilbene heterodimer (10), together with six known (2-7) analogs. Their chemical structures were elucidated by spectroscopic analysis and theoretical NMR and ECD calculations. Compounds 9 and 10 are unique in their scaffolds. The in vitro cytotoxic activity of purified compounds was evaluated against eight tumor cell lines (HCT116, LoVo, DU145, PC3, HEP3B, HEPG2, MCF7, and MDA-MB-231) and one nontumor cell line (L929) by the MTS assay. Compounds 1, 2, 4, and 10 exhibited inhibition with IC50 values ranging from 8.2 to 37.6 μM. Cytotoxic cell death mechanisms were further investigated, indicating variability in apoptosis, necrosis, or cell cycle arrest.

Department of Analytical Chemistry Faculty of Pharmacy Charles University Heyrovského 1203 500 03 Hradec Kralove Czech Republic

Department of Chemistry University of California Davis California 95616 United States

Department of Immunology Faculty of Medicine Yeditepe University TR 34755 Kayışdağı İstanbul Türkiye

Department of Natural Drugs Faculty of Pharmacy Masaryk University Palackého třída 1946 1 61200 Brno Czech Republic

Department of Organic and Bioorganic Chemistry Faculty of Pharmacy Charles University Heyrovského 1203 500 03 Hradec Kralove Czech Republic

Department of Pharmacognosy and Pharmaceutical Botany Faculty of Pharmacy Charles University Heyrovského 1203 500 03 Hradec Kralove Czech Republic

Department of Pharmacognosy Faculty of Pharmacy Yeditepe University TR 34755 Kayışdağı İstanbul Türkiye

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